His second match, happened in July 22, was against rising star Yuki Kondo, whom Schilt would face three more times in his career. In the first of their matches, Kondo showed himself as the better wrestler, but Schilt's size enabled him to power out of his control and win some exchanges. They traded positions until the ring call at 15:00, with Kondo being declared the winner by split decision.

With a short 2–3 record, Schilt was pitted against Pancrase co-founder Masakatsu Funaki on February 22, 1997. After circling around, Funaki scored a takedown, mounted Schilt and worked to an armbar, which Schilt had to spend a rope escape to get out from. Restarted the fight, Schilt reversed a takedown and got his own mount, but Funaki recovered guard and applied a toehold, forcing the karateka to spend another point. The two fighters then passed some minutes clinched on a corner, until Funaki led him to the ground and locked a kneebar from half mount, making Schilt tap out.

On January 16, 1998, he fought the other co-founder of Pancrase, Minoru Suzuki. The Japanese wrestler took Schilt to the mat and kept side control for half of the match, but wasn't able to threaten him from the position aside from scarce armbar attempts, and Schilt eventually capitalized on one of them to escape. The situation repeated itself, but this time Suzuki locked successfully an armbar and Schilt barely reached the ropes to get a escape. Once standing again, however, Schilt went aggressively and landed a clean knee strike to Suzuki's chin, knocking him out for the win.

Schilt got a rematch against Masakatsu Funaki on March 18, 1998, but although he managed to take the bout to the judges, he lost by points due to spent rope escapes.

Months after, on September 14, he had his rubber match against Funaki. This time, the karateka showed himself capable of stopping the wrestler's takedowns, blocking the first of them with the aid of the ropes and a guillotine choke and reversing the second into Funaki's guard. After pressing for some minutes and avoiding a kneebar attempt, Schilt got the fight standing and scored a KO by two clinched knees. Funaki got up and looked to continue the fight, but the Dutch landed another KO, and finally finished him with a combination of knees and palm strikes.

On June 20, 1999, Schilt would fly back to Holland in order to face Gilbert Yvel in an interpromotional match. The bout was particularly intriguing because Yvel belonged to Fighting Network RINGS, Pancrase's rival promotion in Japan. They met under special rules, with Gilbert keeping his gloves for punching while Schilt preferred to go barehanded and use open palm strikes like it was done in Pancrase.

When the match began, Schilt was knocked down by a shocking flurry of hooks from Yvel, but he managed to recover before the eight count. Schilt came back and controlled Gilbert with open palms and knees to the body, but he decided to take the fight to the ground, not wanting to risk another KO from the RINGS muay thai specialist. However, Yvel turned out able to block all of his submission attempts on the mat, in a big part due to the fast stand-ups of the format. At the second round, the RINGS fighter mounted Schilt and illegally eye-gouged him, but it wasn't called by the referee, and Schilt was left with his eye swollen shut. From that point, the two strikers exchanged hits until Yvel overpowered Schilt, landing multiple unanswered punches for the KO stoppage.[10]

Schilt returned for another interpromotional match against RINGS in June 4, 2000, facing Yoshihisa Yamamoto. Schilt won the match in under three minutes after a striking combination.

On November 28, 1999, Schilt won the King of Pancrase openweight championship from Yuki Kondo. He had two successful defenses against Kazuo Takahashi and Osami Shibuya before vacating it due to signing up with UFC.

His second and last appearance in the promotion would be the next event, UFC 32, where Schilt was pitted against Josh Barnett. Schilt was taken down and mounted again, but Barnett was able to land abundant strikes, some of which were answered by Schilt, cutting both of their faces and spilling a large amount of blood on the mat. Eventually, Schilt flipped Barnett over, but Barnett locked an armbar from the guard and made him tap out.[12]

After his UFC tenure, Schilt returned to Japan for PRIDE Fighting Championship, making his debut on September 24, 2001 in PRIDE 16. His opponent was originally Igor Vovchanchyn, but Akira Shoji volunteered to fight him after Vovchanchyn withdrew from the match due to injuries. Shoji took Schilt to the ground, but Schilt reversed him and proceeded to land heavy strikes both on the ground and standing. Schilt finished him with a combination of knee, punch and kick for the KO.[13] Schilt followed with two easy victories over K-1 legend Masaaki Satake and professional wrestler Yoshihiro Takayama, knocking them both out.

On June 23, 2002, Schilt faced Fedor Emelianenko, who was debuting in PRIDE after a solid career in Fighting Network RINGS. Started the match, although Schilt avoided a dangerous armbar attempt, Emelianenko pinned him and scored repeated punches and knees to his face until the end of the round. At the second round, Schilt managed to keep the Russian on his guard and minimize the damage of his ground and pound, but Emelianenko took over again and ended the fight punishing the Ashihara karateka with more punches on the ground. Fedor was declared winner.[14]

Schilt tried to bounce back on November 24, 2002 against Antônio Rodrigo Nogueira. The match was originally a title bout for the PRIDE Heavyweight Champion, but it was changed to a non-title bout due to Schilt's loss to Emelianenko. Capitalizing on his superiority on the ground, the Brazilian pulled guard at several instances and eventually got mount. When Schilt flipped him over, Nogueira feigned an armbar from the guard and then locked a triangle choke, making Schilt tap out in his second loss in PRIDE.[15]

At the end of 2003, he took part in the annual event Inoki Bom-Ba-Ye for a rematch against Josh Barnett. Schilt was defeated again by armbar, this time on the third round.

On 19 November 2005 Schilt made his first appearance at the K-1 finals. Schilt beat Ray Sefo in the quarter finals and the defending champion Remy Bonjasky by knockout in the semifinals. Schilt then met Glaube Feitosa in the tournament finals and won by knockout due to knee strike to win his first K-1 World Grand Prix title.

In the first round of the World Grand Prix 2007 Finals, Schilt was matched against Brazilian Karate fighter Glaube Feitosa. Schilt survived a near knockdown from one of Glaube's famed Brazilian kicks to win by unanimous decision. This marked the third time he had defeated Feitosa in his career.

In the semi finals he met Jerome LeBanner for the second time. Schilt was put on the defensive for most of the first round. Just before time expired, Schilt landed a knee strike which badly hurt LeBanner. Before the second round started, LeBanner was noticeably limping in his corner. Early in the second round, a low kick from Schilt sent him to the canvas in obvious pain. LeBanner was able to make it back to his feet however his corner threw in the towel to avoid further injury.

The final match of the 2007 K-1 World Grand Prix was a rematch from the year before, with Schilt matched up against fellow Dutchman Peter Aerts for the third time. The match came to an abrupt end 1:49 in after Aerts injured his knee and could not continue. With the win Schilt became the third man to win the K-1 World Grand Prix three times, and the only man in history to win three consecutive Grand Prix crowns.

In September 2008, Schilt lost a decision against Peter Aerts at the K-1 World Grand Prix Final 16 in Seoul.

On 16 May 2009, Schilt lost to Badr Hari via first round KO at the Dutch Kickboxing event It's Showtime 2009 Amsterdam, Netherlands. The fight was for the It's Showtime World Heavyweight Title.

The same year he met Badr Hari again at K-1 final and defeated him in 1st round

At the 2009 Final 16 Schilt beat the rising Romanian Daniel Ghita by unanimous decision.[17] At the final selection he chose to fight Jerome LeBanner and went on to defeat him for the fourth time in his career in the first round by KO. In the second round he was matched against Remy Bonjasky, whom he also defeated for the third time by KO in the first round, after getting knocked down himself. In the finals he beat Badr Hari by KO in the first to win his fourth GP title, also getting the record of fastest GP win with a total time over all 3 matches of 355 seconds.[18] With the win he became the second man in history to win the WGP Title four times (Ernesto Hoost being the first).

In April 2010, he successfully made his fourth title defence against teammate Errol Zimmerman by unanimous decision. At the 2010 Final 16 he beat Hesdy Gerges by a close decision, after sustaining a cut to his shin in the fight that required 4 stitches.
In the semi finals of the K-1 World Grand Prix 2010 Final he was defeated for the first time in a tournament by Peter Aerts in a gruelling decision.[19]

In 2012 Schilt returned to the ring with a more aggressive style earning a convincing victory over Guidon and Zimmerman.

At the sixteen-man 2012 Glory Heavyweight Grand Slam at Glory 4: Tokyo - 2012 Heavyweight Grand Slam in Saitama, Japan on 31 December 2012, Schilt rematched Brice Guidon at the first stage of the tournament. He floored the Frenchman with a left jab in the opening seconds of round two before finishing him with the same technique soon after. At the quarter-final stage, he went up against Rico Verhoeven and, as he won the first of the two, two-minute rounds, was given his passage to the semis via unanimous decision. There, he used his eleven-inch height and twenty-seven kilogram weight advantage to outpoint Gokhan Saki to another two-round unanimous points verdict. A highly anticipated match-up with Daniel Ghiţă awaited him in the final and, after a slow start to the three-minute first round, Schilt sent the Romanian bruiser to the canvas with a left high kick. Despite Ghiţă seemingly recovering from the blow, referee Joop Ubeda controversially called a halt to the contest, giving Schilt the TKO win and the inaugural Glory Grand Slam crown.[20][21][22]